AU657529B2 - Reaction products of a boron compound and a phospholipid, and lubricants and aqueous fluids containing same - Google Patents
Reaction products of a boron compound and a phospholipid, and lubricants and aqueous fluids containing sameInfo
- Publication number
- AU657529B2 AU657529B2 AU15583/92A AU1558392A AU657529B2 AU 657529 B2 AU657529 B2 AU 657529B2 AU 15583/92 A AU15583/92 A AU 15583/92A AU 1558392 A AU1558392 A AU 1558392A AU 657529 B2 AU657529 B2 AU 657529B2
- Authority
- AU
- Australia
- Prior art keywords
- composition
- acid
- carboxylic
- phospholipid
- amine
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 150000003904 phospholipids Chemical class 0.000 title claims abstract description 65
- 239000012530 fluid Substances 0.000 title claims abstract description 45
- 150000001639 boron compounds Chemical class 0.000 title claims abstract description 40
- 239000007795 chemical reaction product Substances 0.000 title claims description 40
- 239000000314 lubricant Substances 0.000 title description 34
- 239000000203 mixture Substances 0.000 claims abstract description 206
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 76
- -1 transition metal salt Chemical class 0.000 claims description 140
- 150000001412 amines Chemical class 0.000 claims description 89
- 125000004432 carbon atom Chemical group C* 0.000 claims description 73
- 229910052751 metal Inorganic materials 0.000 claims description 57
- 239000002184 metal Substances 0.000 claims description 57
- 230000007935 neutral effect Effects 0.000 claims description 40
- 239000003921 oil Substances 0.000 claims description 40
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 37
- 150000003839 salts Chemical class 0.000 claims description 35
- 229920000098 polyolefin Polymers 0.000 claims description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 29
- 150000002148 esters Chemical group 0.000 claims description 27
- 230000001050 lubricating effect Effects 0.000 claims description 27
- 125000001424 substituent group Chemical group 0.000 claims description 27
- 150000001735 carboxylic acids Chemical class 0.000 claims description 25
- 150000001733 carboxylic acid esters Chemical class 0.000 claims description 24
- 239000000787 lecithin Substances 0.000 claims description 24
- 235000010445 lecithin Nutrition 0.000 claims description 24
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 19
- 239000002904 solvent Substances 0.000 claims description 19
- 150000002440 hydroxy compounds Chemical class 0.000 claims description 17
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 16
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 16
- 150000002830 nitrogen compounds Chemical class 0.000 claims description 16
- 229940067606 lecithin Drugs 0.000 claims description 15
- 150000007524 organic acids Chemical class 0.000 claims description 15
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
- 239000011575 calcium Substances 0.000 claims description 13
- 229910052791 calcium Inorganic materials 0.000 claims description 13
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 claims description 13
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 12
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 11
- 239000004327 boric acid Substances 0.000 claims description 11
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 10
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 10
- 238000006683 Mannich reaction Methods 0.000 claims description 10
- 229910052728 basic metal Inorganic materials 0.000 claims description 10
- 235000021313 oleic acid Nutrition 0.000 claims description 10
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 9
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 9
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 9
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 9
- 235000021355 Stearic acid Nutrition 0.000 claims description 9
- 230000005540 biological transmission Effects 0.000 claims description 9
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 9
- 239000005642 Oleic acid Substances 0.000 claims description 8
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 8
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 8
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 8
- 239000008117 stearic acid Substances 0.000 claims description 8
- 235000020238 sunflower seed Nutrition 0.000 claims description 8
- 125000002252 acyl group Chemical group 0.000 claims description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims description 7
- 239000012208 gear oil Substances 0.000 claims description 7
- 150000002327 glycerophospholipids Chemical class 0.000 claims description 7
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 7
- 229910019142 PO4 Inorganic materials 0.000 claims description 6
- 235000021314 Palmitic acid Nutrition 0.000 claims description 6
- 240000008042 Zea mays Species 0.000 claims description 6
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 6
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 6
- 239000003513 alkali Substances 0.000 claims description 6
- 235000005822 corn Nutrition 0.000 claims description 6
- 239000010720 hydraulic oil Substances 0.000 claims description 6
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 claims description 6
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 claims description 5
- 244000068988 Glycine max Species 0.000 claims description 5
- 235000010469 Glycine max Nutrition 0.000 claims description 5
- 150000001340 alkali metals Chemical class 0.000 claims description 5
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 5
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 5
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 4
- 229960004488 linolenic acid Drugs 0.000 claims description 4
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 4
- 239000010452 phosphate Substances 0.000 claims description 4
- 150000003905 phosphatidylinositols Chemical class 0.000 claims description 4
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 claims description 4
- PORPENFLTBBHSG-MGBGTMOVSA-N 1,2-dihexadecanoyl-sn-glycerol-3-phosphate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(O)=O)OC(=O)CCCCCCCCCCCCCCC PORPENFLTBBHSG-MGBGTMOVSA-N 0.000 claims description 3
- TZCPCKNHXULUIY-RGULYWFUSA-N 1,2-distearoyl-sn-glycero-3-phosphoserine Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OC[C@H](N)C(O)=O)OC(=O)CCCCCCCCCCCCCCCCC TZCPCKNHXULUIY-RGULYWFUSA-N 0.000 claims description 3
- 235000017060 Arachis glabrata Nutrition 0.000 claims description 3
- 244000105624 Arachis hypogaea Species 0.000 claims description 3
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 3
- 235000018262 Arachis monticola Nutrition 0.000 claims description 3
- 240000002791 Brassica napus Species 0.000 claims description 3
- 235000004977 Brassica sinapistrum Nutrition 0.000 claims description 3
- 235000004936 Bromus mango Nutrition 0.000 claims description 3
- 240000006432 Carica papaya Species 0.000 claims description 3
- 235000009467 Carica papaya Nutrition 0.000 claims description 3
- 244000000626 Daucus carota Species 0.000 claims description 3
- 235000002767 Daucus carota Nutrition 0.000 claims description 3
- ZWZWYGMENQVNFU-UHFFFAOYSA-N Glycerophosphorylserin Natural products OC(=O)C(N)COP(O)(=O)OCC(O)CO ZWZWYGMENQVNFU-UHFFFAOYSA-N 0.000 claims description 3
- 240000005979 Hordeum vulgare Species 0.000 claims description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 claims description 3
- 240000007228 Mangifera indica Species 0.000 claims description 3
- 235000014826 Mangifera indica Nutrition 0.000 claims description 3
- 240000007817 Olea europaea Species 0.000 claims description 3
- 240000007594 Oryza sativa Species 0.000 claims description 3
- 235000007164 Oryza sativa Nutrition 0.000 claims description 3
- 244000025272 Persea americana Species 0.000 claims description 3
- 235000008673 Persea americana Nutrition 0.000 claims description 3
- 235000009184 Spondias indica Nutrition 0.000 claims description 3
- 235000021307 Triticum Nutrition 0.000 claims description 3
- 235000021342 arachidonic acid Nutrition 0.000 claims description 3
- 235000020232 peanut Nutrition 0.000 claims description 3
- WTJKGGKOPKCXLL-RRHRGVEJSA-N phosphatidylcholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCC=CCCCCCCCC WTJKGGKOPKCXLL-RRHRGVEJSA-N 0.000 claims description 3
- 235000009566 rice Nutrition 0.000 claims description 3
- 125000004119 disulfanediyl group Chemical group *SS* 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- VKOBVWXKNCXXDE-UHFFFAOYSA-N icosanoic acid Chemical compound CCCCCCCCCCCCCCCCCCCC(O)=O VKOBVWXKNCXXDE-UHFFFAOYSA-N 0.000 claims 4
- 229920000742 Cotton Polymers 0.000 claims 2
- 241000209140 Triticum Species 0.000 claims 2
- JCABVIFDXFFRMT-DIPNUNPCSA-N [(2r)-1-[ethoxy(hydroxy)phosphoryl]oxy-3-hexadecanoyloxypropan-2-yl] octadec-9-enoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(O)(=O)OCC)OC(=O)CCCCCCCC=CCCCCCCCC JCABVIFDXFFRMT-DIPNUNPCSA-N 0.000 claims 2
- 229940114079 arachidonic acid Drugs 0.000 claims 2
- 239000000463 material Substances 0.000 abstract description 31
- 239000003879 lubricant additive Substances 0.000 abstract description 4
- 230000001580 bacterial effect Effects 0.000 abstract description 2
- 230000003385 bacteriostatic effect Effects 0.000 abstract description 2
- 230000009286 beneficial effect Effects 0.000 abstract description 2
- 239000002253 acid Substances 0.000 description 75
- 229920000768 polyamine Polymers 0.000 description 48
- 239000000047 product Substances 0.000 description 48
- 150000007513 acids Chemical class 0.000 description 47
- 238000006243 chemical reaction Methods 0.000 description 39
- 235000019198 oils Nutrition 0.000 description 28
- 150000001875 compounds Chemical class 0.000 description 25
- 229910052796 boron Inorganic materials 0.000 description 24
- 238000000034 method Methods 0.000 description 24
- 239000002480 mineral oil Substances 0.000 description 24
- 235000010446 mineral oil Nutrition 0.000 description 23
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 22
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 22
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 21
- 229920000642 polymer Polymers 0.000 description 21
- 150000003460 sulfonic acids Chemical class 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
- 239000000654 additive Substances 0.000 description 19
- 125000003118 aryl group Chemical group 0.000 description 19
- 229910052698 phosphorus Inorganic materials 0.000 description 19
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 150000001336 alkenes Chemical class 0.000 description 18
- 239000003153 chemical reaction reagent Substances 0.000 description 18
- 239000011572 manganese Substances 0.000 description 18
- 125000001931 aliphatic group Chemical group 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 239000002562 thickening agent Substances 0.000 description 17
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 16
- 239000011574 phosphorus Substances 0.000 description 16
- 125000000217 alkyl group Chemical group 0.000 description 15
- 150000002989 phenols Chemical class 0.000 description 15
- 230000002378 acidificating effect Effects 0.000 description 14
- 125000002947 alkylene group Chemical group 0.000 description 14
- 229910002092 carbon dioxide Inorganic materials 0.000 description 14
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerol group Chemical group OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 14
- 229910052717 sulfur Inorganic materials 0.000 description 14
- 239000011593 sulfur Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 13
- 235000014113 dietary fatty acids Nutrition 0.000 description 13
- 239000000194 fatty acid Substances 0.000 description 13
- 229930195729 fatty acid Natural products 0.000 description 13
- 239000013538 functional additive Substances 0.000 description 13
- 229930195733 hydrocarbon Natural products 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 150000001298 alcohols Chemical class 0.000 description 12
- 229920001577 copolymer Polymers 0.000 description 12
- 239000002270 dispersing agent Substances 0.000 description 12
- 150000004665 fatty acids Chemical class 0.000 description 12
- 239000004094 surface-active agent Substances 0.000 description 12
- 239000004215 Carbon black (E152) Substances 0.000 description 11
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Substances 0.000 description 11
- 239000003112 inhibitor Substances 0.000 description 11
- 229920001083 polybutene Polymers 0.000 description 11
- 229940014800 succinic anhydride Drugs 0.000 description 11
- FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical class ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 150000002430 hydrocarbons Chemical class 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 159000000007 calcium salts Chemical class 0.000 description 9
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 9
- 239000000376 reactant Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 239000005977 Ethylene Substances 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 239000012141 concentrate Substances 0.000 description 8
- 229940093470 ethylene Drugs 0.000 description 8
- 239000010687 lubricating oil Substances 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 8
- 229910052753 mercury Inorganic materials 0.000 description 8
- 239000011734 sodium Substances 0.000 description 8
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 7
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 7
- 150000008064 anhydrides Chemical class 0.000 description 7
- 230000000844 anti-bacterial effect Effects 0.000 description 7
- 239000002518 antifoaming agent Substances 0.000 description 7
- 239000003899 bactericide agent Substances 0.000 description 7
- 150000002894 organic compounds Chemical class 0.000 description 7
- 229910052760 oxygen Inorganic materials 0.000 description 7
- 239000001301 oxygen Substances 0.000 description 7
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 150000005846 sugar alcohols Polymers 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 6
- 229920002367 Polyisobutene Chemical class 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 6
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- 238000002360 preparation method Methods 0.000 description 6
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- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 description 6
- 229910052725 zinc Inorganic materials 0.000 description 6
- 239000011701 zinc Substances 0.000 description 6
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 5
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- VKCLPVFDVVKEKU-UHFFFAOYSA-N S=[P] Chemical compound S=[P] VKCLPVFDVVKEKU-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 5
- 150000001408 amides Chemical class 0.000 description 5
- 229910021529 ammonia Inorganic materials 0.000 description 5
- 239000003945 anionic surfactant Substances 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 229920001400 block copolymer Polymers 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003093 cationic surfactant Substances 0.000 description 5
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 5
- 229940012017 ethylenediamine Drugs 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical group O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 150000002763 monocarboxylic acids Chemical class 0.000 description 5
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 5
- 235000021317 phosphate Nutrition 0.000 description 5
- 235000011007 phosphoric acid Nutrition 0.000 description 5
- 229960004838 phosphoric acid Drugs 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 5
- 230000008719 thickening Effects 0.000 description 5
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 4
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid group Chemical group C(CCCCCCCCC(=O)O)(=O)O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
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- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
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- 239000003381 stabilizer Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical class ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 1
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Inorganic materials O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 1
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- 238000010408 sweeping Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 150000000000 tetracarboxylic acids Chemical class 0.000 description 1
- 229940095068 tetradecene Drugs 0.000 description 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
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- 150000003553 thiiranes Chemical class 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
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- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- FAQYAMRNWDIXMY-UHFFFAOYSA-N trichloroborane Chemical compound ClB(Cl)Cl FAQYAMRNWDIXMY-UHFFFAOYSA-N 0.000 description 1
- VQOXUMQBYILCKR-UHFFFAOYSA-N tridecaene Natural products CCCCCCCCCCCC=C VQOXUMQBYILCKR-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-I triphosphate(5-) Chemical compound [O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O UNXRWKVEANCORM-UHFFFAOYSA-I 0.000 description 1
- MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
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- 235000010493 xanthan gum Nutrition 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- DAVUUYDCROAHDW-UHFFFAOYSA-L zinc;6-methylheptoxy-(6-methylheptylsulfanyl)-oxido-sulfanylidene-$l^{5}-phosphane Chemical compound [Zn+2].CC(C)CCCCCOP([O-])(=S)SCCCCCC(C)C.CC(C)CCCCCOP([O-])(=S)SCCCCCC(C)C DAVUUYDCROAHDW-UHFFFAOYSA-L 0.000 description 1
- OECQDNKCDGGPFY-UHFFFAOYSA-L zinc;bis(2-ethylhexoxy)-sulfanylidene-sulfido-$l^{5}-phosphane Chemical compound [Zn+2].CCCCC(CC)COP([S-])(=S)OCC(CC)CCCC.CCCCC(CC)COP([S-])(=S)OCC(CC)CCCC OECQDNKCDGGPFY-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C10M159/00—Lubricating compositions characterised by the additive being of unknown or incompletely defined constitution
- C10M159/12—Reaction products
- C10M159/123—Reaction products obtained by phosphorus or phosphorus-containing compounds, e.g. P x S x with organic compounds
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/04—Hydroxy compounds
- C10M129/10—Hydroxy compounds having hydroxy groups bound to a carbon atom of a six-membered aromatic ring
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- C10M129/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen
- C10M129/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing oxygen having a carbon chain of less than 30 atoms
- C10M129/68—Esters
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of less than 30 atoms
- C10M133/04—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M133/12—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring
- C10M133/14—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to a carbon atom of a six-membered aromatic ring containing hydroxy groups
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
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- C10M133/16—Amides; Imides
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
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- C10M133/38—Heterocyclic nitrogen compounds
- C10M133/44—Five-membered ring containing nitrogen and carbon only
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- C10M133/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen
- C10M133/52—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing nitrogen having a carbon chain of 30 or more atoms
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- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/02—Sulfurised compounds
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- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium containing a sulfur-to-oxygen bond
- C10M135/10—Sulfonic acids or derivatives thereof
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- C10M135/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing sulfur, selenium or tellurium
- C10M135/32—Heterocyclic sulfur, selenium or tellurium compounds
- C10M135/36—Heterocyclic sulfur, selenium or tellurium compounds the ring containing sulfur and carbon with nitrogen or oxygen
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- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
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- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/08—Ammonium or amine salts
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- C10M137/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus
- C10M137/02—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing phosphorus having no phosphorus-to-carbon bond
- C10M137/04—Phosphate esters
- C10M137/10—Thio derivatives
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- C10M139/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing atoms of elements not provided for in groups C10M127/00 - C10M137/00
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- C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
- C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
- C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
- C10M145/14—Acrylate; Methacrylate
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- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
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- C10M155/00—Lubricating compositions characterised by the additive being a macromolecular compound containing atoms of elements not provided for in groups C10M143/00 - C10M153/00
- C10M155/02—Monomer containing silicon
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
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Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US68727191A | 1991-04-18 | 1991-04-18 | |
US687271 | 1991-04-18 | ||
PCT/US1992/001553 WO1992018586A1 (en) | 1991-04-18 | 1992-02-27 | Reaction products of a boron compound and a phospholipid, and lubricants and aqueous fluids containing same |
Publications (2)
Publication Number | Publication Date |
---|---|
AU1558392A AU1558392A (en) | 1992-11-17 |
AU657529B2 true AU657529B2 (en) | 1995-03-16 |
Family
ID=24759760
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
AU15583/92A Ceased AU657529B2 (en) | 1991-04-18 | 1992-02-27 | Reaction products of a boron compound and a phospholipid, and lubricants and aqueous fluids containing same |
Country Status (13)
Country | Link |
---|---|
US (1) | US5487838A (fi) |
EP (1) | EP0540700B1 (fi) |
JP (1) | JPH05509357A (fi) |
AT (1) | ATE169665T1 (fi) |
AU (1) | AU657529B2 (fi) |
BR (1) | BR9205243A (fi) |
CA (1) | CA2085000C (fi) |
DE (1) | DE69226601T2 (fi) |
ES (1) | ES2122992T3 (fi) |
FI (1) | FI925738A (fi) |
MX (1) | MX9201750A (fi) |
NO (1) | NO924904D0 (fi) |
WO (1) | WO1992018586A1 (fi) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BR9304049A (pt) * | 1992-11-12 | 1994-05-17 | Lubrizol Corp | Composição de graxa e método para aumentar o ponto de gotejamento de uma graxa. |
US6302209B1 (en) | 1997-09-10 | 2001-10-16 | Bj Services Company | Surfactant compositions and uses therefor |
US6525004B1 (en) * | 2001-05-01 | 2003-02-25 | Infineum International Inc. | Combustion improving additive for small engine lubricating oils |
US20030199400A1 (en) * | 2002-01-07 | 2003-10-23 | Black Robert H. | Household lubricant and method of use |
WO2005041904A2 (en) * | 2003-10-31 | 2005-05-12 | Fulcrum Pharmaceuticals, Inc. | Inhibitors of coronavirus protease and methods of use thereof |
GB2408748B (en) * | 2004-02-05 | 2006-12-13 | Niche Products Ltd | Hydraulic fluids containing Lecithin |
US7235515B2 (en) * | 2004-02-11 | 2007-06-26 | Ibnsina Karkenny | Method of making a lubrication additive |
JP4996872B2 (ja) * | 2006-03-30 | 2012-08-08 | 協同油脂株式会社 | 金属加工用油剤組成物、金属加工方法及び金属加工品 |
GB2438402B (en) * | 2006-05-22 | 2011-06-01 | Niche Products Ltd | Improvements in and relating to hydraulic fluids |
US8445417B2 (en) * | 2007-12-06 | 2013-05-21 | The Lubrizol Corporation | Lubricating composition containing borated phospholipid |
US8759265B2 (en) * | 2008-07-15 | 2014-06-24 | Ian D. Smith | Thermally stable subsea control hydraulic fluid compositions |
US8575077B2 (en) * | 2008-07-15 | 2013-11-05 | Ian D. Smith | Environmental subsea control hydraulic fluid compositions |
US8633141B2 (en) * | 2008-07-15 | 2014-01-21 | Ian D. Smith | Thermally stable subsea control hydraulic fluid compositions |
US9096812B2 (en) | 2008-07-15 | 2015-08-04 | Macdermid Offshore Solutions, Llc | Environmental subsea control hydraulic fluid compositions |
WO2010048244A1 (en) | 2008-10-23 | 2010-04-29 | The Lubrizol Corporation | Lubricating composition containing metal carboxylate |
US20120172265A1 (en) | 2008-12-09 | 2012-07-05 | The Lubrizol Corporation | Lubricating Composition Containing a Compound Derived from a Hydroxy-carboxylic Acid |
JP5561881B2 (ja) | 2009-05-13 | 2014-07-30 | ザ ルブリゾル コーポレイション | リンゴ酸誘導体を含む潤滑組成物 |
CA2774273A1 (en) | 2009-09-16 | 2011-03-24 | The Lubrizol Corporation | Lubricating composition containing a diester of adipic acid |
CA2800503A1 (en) | 2010-05-24 | 2011-12-01 | The Lubrizol Corporation | Lubricating composition |
JP2012036344A (ja) * | 2010-08-11 | 2012-02-23 | Nisshin Oillio Group Ltd | 潤滑油組成物 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3284409A (en) * | 1965-06-22 | 1966-11-08 | Lubrizol Corp | Substituted succinic acid-boron-alkylene amine phosphatide derived additive and lubricating oil containing same |
GB2125431A (en) * | 1982-08-03 | 1984-03-07 | Karonite Chem Co Ltd | Lubricating oils with boric acid esters |
EP0325977A1 (en) * | 1988-01-27 | 1989-08-02 | The Elco Corporation | Phosphite amine lubricant additives |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2257601A (en) * | 1938-08-06 | 1941-09-30 | Texas Co | Method of lubrication |
US2408090A (en) * | 1940-09-30 | 1946-09-24 | Musher Foundation Inc | Lubricating oils |
US2295192A (en) * | 1940-10-26 | 1942-09-08 | Standard Oil Co | Lubricating composition and modified addition agents for the same |
US2270241A (en) * | 1940-10-30 | 1942-01-20 | Standard Oil Co | Lubricating oil |
US2465733A (en) * | 1943-12-31 | 1949-03-29 | Levis Irene Becker | Lecithin-metal compound |
US2373733A (en) * | 1944-05-27 | 1945-04-17 | Standard Oil Co | Steam cylinder lubricants |
US3085100A (en) * | 1960-12-05 | 1963-04-09 | Staley Mfg Co A E | Oxyalkylated lecithin |
US3252908A (en) * | 1963-11-07 | 1966-05-24 | Lubrizol Corp | Lubricating oil and additive composition |
US4305853A (en) * | 1980-03-11 | 1981-12-15 | American Lecithin Company | Chemical modification of metal oxides and lecithin materials |
US4522629A (en) * | 1983-09-23 | 1985-06-11 | Mobil Oil Corporation | Borated phosphonates as lubricant and fuel additives |
US4529528A (en) * | 1983-12-14 | 1985-07-16 | Mobil Oil Corporation | Borated amine-phosphite reaction product and lubricant and fuel containing same |
US4536306A (en) * | 1983-12-14 | 1985-08-20 | Mobil Oil Corporation | Borated phosphorus-containing compounds and lubricant compositions containing same |
US4557844A (en) * | 1984-01-30 | 1985-12-10 | Mobil Oil Corporation | Aminated boron- and phosphorus-containing compounds and lubricant or fuel compositions containing same |
US4599191A (en) * | 1984-05-01 | 1986-07-08 | Mobil Oil Corporation | Friction reducing additives and compositions thereof |
-
1992
- 1992-02-27 CA CA002085000A patent/CA2085000C/en not_active Expired - Fee Related
- 1992-02-27 ES ES92908016T patent/ES2122992T3/es not_active Expired - Lifetime
- 1992-02-27 BR BR9205243A patent/BR9205243A/pt not_active Application Discontinuation
- 1992-02-27 EP EP92908016A patent/EP0540700B1/en not_active Expired - Lifetime
- 1992-02-27 WO PCT/US1992/001553 patent/WO1992018586A1/en active IP Right Grant
- 1992-02-27 AT AT92908016T patent/ATE169665T1/de not_active IP Right Cessation
- 1992-02-27 DE DE69226601T patent/DE69226601T2/de not_active Expired - Fee Related
- 1992-02-27 AU AU15583/92A patent/AU657529B2/en not_active Ceased
- 1992-02-27 JP JP4507566A patent/JPH05509357A/ja active Pending
- 1992-04-14 MX MX9201750A patent/MX9201750A/es unknown
- 1992-12-17 FI FI925738A patent/FI925738A/fi unknown
- 1992-12-17 NO NO924904A patent/NO924904D0/no unknown
-
1994
- 1994-03-28 US US08/218,860 patent/US5487838A/en not_active Expired - Lifetime
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3284409A (en) * | 1965-06-22 | 1966-11-08 | Lubrizol Corp | Substituted succinic acid-boron-alkylene amine phosphatide derived additive and lubricating oil containing same |
GB2125431A (en) * | 1982-08-03 | 1984-03-07 | Karonite Chem Co Ltd | Lubricating oils with boric acid esters |
EP0325977A1 (en) * | 1988-01-27 | 1989-08-02 | The Elco Corporation | Phosphite amine lubricant additives |
Also Published As
Publication number | Publication date |
---|---|
CA2085000C (en) | 2002-10-08 |
DE69226601D1 (de) | 1998-09-17 |
ES2122992T3 (es) | 1999-01-01 |
JPH05509357A (ja) | 1993-12-22 |
DE69226601T2 (de) | 1999-04-29 |
EP0540700B1 (en) | 1998-08-12 |
FI925738A0 (fi) | 1992-12-17 |
BR9205243A (pt) | 1993-07-27 |
NO924904L (no) | 1992-12-17 |
ATE169665T1 (de) | 1998-08-15 |
MX9201750A (es) | 1992-10-01 |
CA2085000A1 (en) | 1992-10-19 |
US5487838A (en) | 1996-01-30 |
FI925738A (fi) | 1992-12-17 |
EP0540700A1 (en) | 1993-05-12 |
NO924904D0 (no) | 1992-12-17 |
WO1992018586A1 (en) | 1992-10-29 |
AU1558392A (en) | 1992-11-17 |
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